Allylamine → HCID 10193592, compound

Participants

Reaction Steps

To a flame-dried flask under nitrogen was added allylamine (0.60 mL, 8.05 mmol). The flask was cooled in an ice bath, and a solution of (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarbonyl chloride (EXAMPLE 435, Step 2, 0.805 mmol theory) in anhydrous tetrahydrofuran (8.0 mL) was added. The resulting mixture was stirred under nitrogen for 2 hours, allowing the cooling bath to slowly expire, and was then diluted with water (10 mL) and extracted with methylene chloride (20 mL). The organic phase was washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (0.5/99.5-2/98). Pooling and concentration of those fractions with an Rf=0.44 by TLC (methanol/chloroform, 5/95) provides the title compound, mp 167-169° C.; MS (ESI+) for C17H20FN3O4 m/z 350 (M+H)+; [α]25D=−44° (c 0.94, DMSO).

Provenance & Evidence